This invention relates to adamantane derivatives which have the structure: ##STR23## substituted at least at the "2", "4" and "8" positions, thusly: (a) at the "2" position with an oxygen atom;
(b) at the "4" position with a carbon atom; and PA1 (c) at the "8" position with a methyl group
and uses thereof in augmenting or enhancing the aroma or taste of consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting, substantive and intense sandelwood, woody, patchouli, rhubarb, ginger, minty, amyris, camphoraceous, cardamon, earthy, cedarwood-like, vetiver, peppery, grapefruit peel-like, rose-like, ambery, spicy, ginger root, rosemary, piney, chrysanthemon-like, green and fir balsam-like aromas with sweet, amyris, camphoraceous, patchouli, woody, piney, cedarwood, sandalwood, herbaceous, incense, olibanum, vetiver, grapefruit peel-like, floral, sweet pea, rose, peony, fruity, early morning forest path, green, ginger root and amber topnotes are desirable in several types of perfume compositions, perfumed articles, colognes, deodorizing compositions and odor maskant materials.
The use of tricyclic alcohol derivatives in perfumery for augmenting or enhancing the aromas of perfume compositions, perfumed articles and colognes is well known in the art. Thus, Inamoto, et al in U.S. Pat. No. 4,036,893 discloses the use in perfumery of the compound having the structure: ##STR24## Inamoto, et al in U.S. Pat. No. 4,169,958 also discloses the use of the tricyclic alcohol having the structure: ##STR25## in perfumery. Light, et al in U.S. Pat. No. 3,996,169 discloses the use of compound having the structure: ##STR26## in perfumery. Inamoto, et al in U.S. Pat. No. 4,169,958 also discloses the use of the tricyclic alcohol having the structure: ##STR27## in perfumery. Light, et al in U.S. Pat. No. 3,996,169 discloses the use of the compound having the structure: ##STR28## in perfumery. Inamoto, et al in U.S. Pat. No. 4,036,892 discloses the use of the compound having the structure: ##STR29## and in U.S. Pat. No. 4,036,892 discloses the use in perfumery of the compound having the structure: ##STR30## The use in perfumery of the compound having the structure: ##STR31## is disclosed in Chemical Abstracts, Volume 109, 9, 1988, No. 6759v (abstract of Koltsa, et al Zh.Obshch.Khim., 1987, 57 (11) 2620-9.
Light, et al at U.S. Pat. No. 4,439,354 discloses the genus of compounds defined according to the structure: ##STR32## for use in perfumery wherein R.sub.1 represents hydrogen, methyl or acetyl and R.sub.2, R.sub.3, R.sub.4 and R.sub.5 each represent hydrogen, methyl or ethyl.
Light, et al at U.S. Pat. No. 3,996,169 discloses the genus of compounds defined according to the structure: ##STR33## where one or more of the R groups represents hydrogen or methyl.
Adamantane derivatives and adamantane itself are known for use in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes. Thus, the perfume use of compounds having the structures: ##STR34## is disclosed in Chemical Abstracts, Volume 71, No. 94695w (abstract of Netherlands Published Application 6715903, May 28, 1969). Japan Kokai 75/25742 Published on Mar. 18, 1975 and abstracted at Chem.Abstracts, Volume 84, No. 35214j and Japan Kokai Tokkyo Koho 78:145920 Published on Dec. 19, 1978 and abstracted at Chem.Abstracts, Volume 90, No. 142085p discloses the perfume use of adamantane itself having the structure: ##STR35##
Synthesis of various oxygen-substituted adamantane derivatives is well known in the prior art.
Mlinaric'-Magerski and Magerski, J. Am. Chem. Soc., 1983, 105, pages 7389-7395 discloses the compound having the structure: ##STR36## at page 7390 and discloses the reaction squence: ##STR37## at page 7389.
Hallden-Aberton, J. Org. Chem., Volume 46, No. 3, 1981, pages 538-546 discloses the reaction sequence: ##STR38## at pages 539 and 544.
Drivas & Mison, Tetrahedron Letters, Volume 22, 1981, at pages 641-644 discloses at page 643 the reaction sequence: ##STR39##
Kovalev, et al, Chem. Abstracts, Volume 109, 1988, No. 22553d (abstract of Zh.Org.Khim., 1987, 23(9), 1882-6 discloses the compounds having the structures: ##STR40## and discloses the reaction sequence: ##STR41##
However, the adamantane derivatives of our invention have unexpected, unobvious and advantageous properties with respect to the compounds of the prior art. Nothing in the prior art explicitly or implicitly sets forth the adamantane derivatives of our invention or their uses.